Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805037955/bt6783sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805037955/bt6783Isup2.hkl |
CCDC reference: 293839
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.006 Å
- Disorder in main residue
- R factor = 0.033
- wR factor = 0.077
- Data-to-parameter ratio = 8.8
checkCIF/PLATON results
No syntax errors found
Alert level A PLAT431_ALERT_2_A Short Inter HL..A Contact F1 .. F3' .. 2.42 Ang.
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.88 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C14 PLAT301_ALERT_3_C Main Residue Disorder ......................... 3.00 Perc. PLAT322_ALERT_2_C Check Hybridisation of S1 in Main Residue . ? PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6 PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond C13 - C14 ... 1.37 Ang. PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond C14 - C15 ... 1.37 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact C3 .. F3' .. 2.90 Ang. PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 9.20 Deg. C14 -F3 -H14A 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 3.60 Deg. F3 -C14 -H14A 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 7.40 Deg. F3' -C18 -H18A 1.555 1.555 1.555 PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su .. 0.08
Alert level G REFLT03_ALERT_4_G WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure From the CIF: _diffrn_reflns_theta_max 26.34 From the CIF: _reflns_number_total 2348 Count of symmetry unique reflns 1816 Completeness (_total/calc) 129.30% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 532 Fraction of Friedel pairs measured 0.293 Are heavy atom types Z>Si present yes
1 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 14 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 11 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.
C18H10F3N5OS | F(000) = 816 |
Mr = 401.37 | Dx = 1.501 Mg m−3 |
Monoclinic, Cc | Mo Kα radiation, λ = 0.71073 Å |
a = 6.986 (2) Å | Cell parameters from 1764 reflections |
b = 24.629 (7) Å | θ = 3.0–23.7° |
c = 10.333 (3) Å | µ = 0.23 mm−1 |
β = 92.399 (5)° | T = 294 K |
V = 1776.3 (9) Å3 | Plate, colorless |
Z = 4 | 0.26 × 0.22 × 0.16 mm |
Bruker SMART CCD area-detector diffractometer | 2348 independent reflections |
Radiation source: fine-focus sealed tube | 1770 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.032 |
φ and ω scans | θmax = 26.3°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −8→8 |
Tmin = 0.942, Tmax = 0.964 | k = −30→27 |
4739 measured reflections | l = −6→12 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.033 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.077 | w = 1/[σ2(Fo2) + (0.0402P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
2348 reflections | Δρmax = 0.14 e Å−3 |
267 parameters | Δρmin = −0.21 e Å−3 |
4 restraints | Absolute structure: Flack (1983), 547 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.00 (8) |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
S1 | 0.67979 (11) | 0.91503 (3) | 0.02177 (9) | 0.0446 (2) | |
F1 | 0.8945 (3) | 1.22209 (8) | 0.2711 (3) | 0.0907 (9) | |
F2 | 0.4278 (3) | 1.09395 (8) | 0.1507 (3) | 0.0813 (8) | |
O1 | 0.4150 (4) | 0.83399 (10) | 0.0388 (3) | 0.0626 (8) | |
N1 | 0.3856 (4) | 0.90125 (11) | 0.1855 (3) | 0.0402 (7) | |
H1 | 0.312 (4) | 0.9208 (12) | 0.243 (3) | 0.048 (10)* | |
N2 | 0.5473 (4) | 0.98416 (10) | 0.1853 (3) | 0.0378 (6) | |
N3 | 0.9416 (3) | 0.99340 (10) | −0.0357 (3) | 0.0375 (7) | |
N4 | 1.1112 (4) | 0.96503 (12) | −0.0230 (3) | 0.0522 (8) | |
N5 | 1.1382 (4) | 1.03805 (11) | −0.1540 (3) | 0.0462 (7) | |
C1 | 0.9405 (5) | 1.08122 (13) | 0.1868 (4) | 0.0478 (9) | |
H1A | 1.0367 | 1.0555 | 0.1785 | 0.057* | |
C2 | 0.9891 (5) | 1.13361 (15) | 0.2230 (4) | 0.0559 (10) | |
H2 | 1.1166 | 1.1432 | 0.2395 | 0.067* | |
C3 | 0.8470 (6) | 1.17090 (13) | 0.2341 (4) | 0.0570 (10) | |
C4 | 0.6583 (6) | 1.15855 (14) | 0.2122 (4) | 0.0601 (11) | |
H4 | 0.5632 | 1.1845 | 0.2216 | 0.072* | |
C5 | 0.6140 (5) | 1.10656 (14) | 0.1759 (4) | 0.0469 (9) | |
C6 | 0.7495 (4) | 1.06606 (12) | 0.1622 (3) | 0.0373 (8) | |
C7 | 0.6964 (4) | 1.01004 (12) | 0.1257 (3) | 0.0356 (8) | |
C8 | 0.5251 (4) | 0.93498 (12) | 0.1399 (3) | 0.0365 (8) | |
C9 | 0.7837 (4) | 0.97867 (12) | 0.0383 (3) | 0.0365 (8) | |
C10 | 0.9626 (5) | 1.03592 (13) | −0.1127 (4) | 0.0450 (9) | |
H10 | 0.8665 | 1.0608 | −0.1345 | 0.054* | |
C11 | 1.2198 (5) | 0.99421 (16) | −0.0967 (4) | 0.0526 (10) | |
H11 | 1.3470 | 0.9851 | −0.1088 | 0.063* | |
C12 | 0.3331 (5) | 0.85369 (12) | 0.1299 (4) | 0.0436 (9) | |
F3 | 0.2740 (5) | 0.83953 (12) | 0.4006 (3) | 0.0901 (13) | 0.896 (8) |
F3' | 0.055 (4) | 0.8032 (12) | −0.0252 (13) | 0.111 (13) | 0.104 (8) |
C13 | 0.1614 (5) | 0.82774 (13) | 0.1862 (4) | 0.0467 (9) | |
C14 | 0.1359 (6) | 0.82332 (15) | 0.3166 (4) | 0.0607 (11) | |
H14A | 0.2342 | 0.8373 | 0.3751 | 0.073* | 0.104 (8) |
C15 | −0.0241 (8) | 0.80027 (18) | 0.3661 (6) | 0.0928 (18) | |
H15A | −0.0363 | 0.7971 | 0.4551 | 0.111* | |
C16 | −0.1653 (8) | 0.7820 (2) | 0.2811 (9) | 0.103 (2) | |
H16A | −0.2766 | 0.7675 | 0.3133 | 0.124* | |
C17 | −0.1467 (6) | 0.78448 (17) | 0.1505 (8) | 0.0905 (18) | |
H17A | −0.2434 | 0.7713 | 0.0945 | 0.109* | |
C18 | 0.0187 (6) | 0.80700 (15) | 0.1013 (6) | 0.0675 (12) | |
H18A | 0.0337 | 0.8082 | 0.0124 | 0.081* | 0.896 (8) |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0406 (5) | 0.0422 (4) | 0.0526 (5) | 0.0006 (4) | 0.0212 (4) | −0.0045 (4) |
F1 | 0.0797 (17) | 0.0422 (12) | 0.150 (3) | −0.0062 (11) | −0.0029 (18) | −0.0159 (13) |
F2 | 0.0340 (12) | 0.0669 (15) | 0.143 (3) | 0.0102 (10) | 0.0019 (14) | −0.0125 (14) |
O1 | 0.0613 (17) | 0.0576 (14) | 0.0707 (19) | −0.0064 (13) | 0.0239 (15) | −0.0173 (14) |
N1 | 0.0332 (15) | 0.0388 (15) | 0.0498 (19) | −0.0029 (12) | 0.0170 (14) | −0.0023 (13) |
N2 | 0.0313 (14) | 0.0386 (15) | 0.0445 (16) | −0.0005 (11) | 0.0121 (13) | 0.0006 (13) |
N3 | 0.0284 (14) | 0.0406 (15) | 0.0446 (17) | 0.0057 (11) | 0.0155 (13) | 0.0042 (13) |
N4 | 0.0391 (17) | 0.0627 (19) | 0.056 (2) | 0.0126 (14) | 0.0164 (15) | 0.0153 (15) |
N5 | 0.0367 (15) | 0.0541 (18) | 0.0490 (17) | −0.0021 (14) | 0.0162 (14) | 0.0059 (15) |
C1 | 0.0368 (19) | 0.044 (2) | 0.063 (3) | 0.0051 (16) | 0.0093 (18) | 0.0001 (19) |
C2 | 0.039 (2) | 0.053 (2) | 0.075 (3) | −0.0067 (17) | 0.003 (2) | −0.002 (2) |
C3 | 0.057 (2) | 0.0353 (19) | 0.079 (3) | −0.0033 (16) | 0.008 (2) | 0.0026 (18) |
C4 | 0.049 (2) | 0.042 (2) | 0.090 (3) | 0.0134 (17) | 0.014 (2) | −0.002 (2) |
C5 | 0.0311 (19) | 0.049 (2) | 0.060 (2) | 0.0032 (15) | 0.0059 (18) | 0.0019 (18) |
C6 | 0.0306 (17) | 0.0385 (17) | 0.044 (2) | 0.0019 (14) | 0.0125 (15) | 0.0009 (15) |
C7 | 0.0273 (17) | 0.0414 (18) | 0.039 (2) | 0.0029 (13) | 0.0082 (15) | 0.0057 (15) |
C8 | 0.0294 (16) | 0.0386 (18) | 0.042 (2) | 0.0066 (14) | 0.0072 (16) | 0.0012 (14) |
C9 | 0.0328 (18) | 0.0362 (18) | 0.041 (2) | 0.0021 (13) | 0.0112 (16) | 0.0026 (14) |
C10 | 0.041 (2) | 0.0483 (19) | 0.047 (2) | 0.0050 (16) | 0.0136 (17) | 0.0027 (17) |
C11 | 0.0314 (19) | 0.078 (3) | 0.049 (2) | 0.0037 (19) | 0.0154 (18) | 0.010 (2) |
C12 | 0.0375 (19) | 0.0370 (18) | 0.057 (2) | 0.0032 (15) | 0.0077 (18) | −0.0016 (17) |
F3 | 0.117 (3) | 0.096 (2) | 0.0570 (19) | −0.0387 (18) | 0.0032 (18) | 0.0041 (15) |
F3' | 0.13 (3) | 0.11 (2) | 0.09 (2) | −0.057 (19) | −0.025 (19) | −0.006 (17) |
C13 | 0.0362 (19) | 0.0369 (18) | 0.068 (3) | −0.0035 (15) | 0.0097 (19) | −0.0004 (18) |
C14 | 0.062 (3) | 0.054 (2) | 0.068 (3) | −0.009 (2) | 0.021 (2) | −0.003 (2) |
C15 | 0.104 (4) | 0.072 (3) | 0.107 (4) | −0.024 (3) | 0.055 (4) | 0.000 (3) |
C16 | 0.067 (3) | 0.071 (3) | 0.176 (7) | −0.015 (3) | 0.049 (4) | 0.011 (4) |
C17 | 0.046 (3) | 0.055 (3) | 0.168 (6) | −0.009 (2) | −0.015 (3) | 0.014 (3) |
C18 | 0.053 (2) | 0.051 (2) | 0.097 (4) | −0.006 (2) | −0.009 (3) | 0.003 (2) |
S1—C9 | 1.733 (3) | C4—C5 | 1.366 (5) |
S1—C8 | 1.734 (3) | C4—H4 | 0.9300 |
F1—C3 | 1.355 (4) | C5—C6 | 1.386 (4) |
F2—C5 | 1.352 (4) | C6—C7 | 1.474 (4) |
O1—C12 | 1.222 (4) | C7—C9 | 1.353 (4) |
N1—C12 | 1.349 (4) | C10—H10 | 0.9300 |
N1—C8 | 1.379 (4) | C11—H11 | 0.9300 |
N1—H1 | 0.94 (3) | C12—C13 | 1.498 (4) |
N2—C8 | 1.306 (4) | F3—C14 | 1.332 (5) |
N2—C7 | 1.387 (4) | F3—H14A | 0.3788 |
N3—C10 | 1.327 (4) | F3'—C18 | 1.346 (10) |
N3—N4 | 1.377 (4) | C13—C14 | 1.371 (6) |
N3—C9 | 1.415 (4) | C13—C18 | 1.396 (6) |
N4—C11 | 1.312 (4) | C14—C15 | 1.371 (6) |
N5—C10 | 1.317 (4) | C14—H14A | 0.9599 |
N5—C11 | 1.347 (5) | C15—C16 | 1.369 (9) |
C1—C2 | 1.382 (5) | C15—H15A | 0.9300 |
C1—C6 | 1.398 (5) | C16—C17 | 1.363 (8) |
C1—H1A | 0.9300 | C16—H16A | 0.9300 |
C2—C3 | 1.361 (5) | C17—C18 | 1.396 (6) |
C2—H2 | 0.9300 | C17—H17A | 0.9300 |
C3—C4 | 1.362 (5) | C18—H18A | 0.9300 |
C9—S1—C8 | 86.86 (14) | N3—C9—S1 | 120.8 (2) |
C12—N1—C8 | 124.1 (3) | N5—C10—N3 | 110.7 (3) |
C12—N1—H1 | 124.7 (19) | N5—C10—H10 | 124.6 |
C8—N1—H1 | 108.9 (19) | N3—C10—H10 | 124.6 |
C8—N2—C7 | 110.3 (2) | N4—C11—N5 | 116.8 (3) |
C10—N3—N4 | 109.9 (2) | N4—C11—H11 | 121.6 |
C10—N3—C9 | 129.4 (3) | N5—C11—H11 | 121.6 |
N4—N3—C9 | 120.4 (2) | O1—C12—N1 | 123.1 (3) |
C11—N4—N3 | 100.6 (3) | O1—C12—C13 | 122.5 (3) |
C10—N5—C11 | 102.0 (3) | N1—C12—C13 | 114.4 (3) |
C2—C1—C6 | 121.4 (3) | C14—F3—H14A | 9.2 |
C2—C1—H1A | 119.3 | C14—C13—C18 | 118.0 (4) |
C6—C1—H1A | 119.3 | C14—C13—C12 | 123.7 (4) |
C3—C2—C1 | 118.7 (3) | C18—C13—C12 | 118.3 (4) |
C3—C2—H2 | 120.6 | F3—C14—C13 | 119.8 (3) |
C1—C2—H2 | 120.6 | F3—C14—C15 | 117.4 (5) |
F1—C3—C2 | 118.7 (3) | C13—C14—C15 | 122.8 (5) |
F1—C3—C4 | 118.6 (3) | F3—C14—H14A | 3.6 |
C2—C3—C4 | 122.7 (3) | C13—C14—H14A | 118.1 |
C3—C4—C5 | 117.5 (3) | C15—C14—H14A | 119.1 |
C3—C4—H4 | 121.3 | C16—C15—C14 | 118.2 (6) |
C5—C4—H4 | 121.3 | C16—C15—H15A | 120.9 |
F2—C5—C4 | 118.2 (3) | C14—C15—H15A | 120.9 |
F2—C5—C6 | 118.1 (3) | C17—C16—C15 | 121.6 (5) |
C4—C5—C6 | 123.7 (3) | C17—C16—H16A | 119.2 |
C5—C6—C1 | 116.1 (3) | C15—C16—H16A | 119.2 |
C5—C6—C7 | 122.3 (3) | C16—C17—C18 | 119.5 (6) |
C1—C6—C7 | 121.6 (3) | C16—C17—H17A | 120.2 |
C9—C7—N2 | 113.7 (3) | C18—C17—H17A | 120.2 |
C9—C7—C6 | 126.2 (3) | F3'—C18—C17 | 121.4 (13) |
N2—C7—C6 | 120.1 (2) | F3'—C18—C13 | 118.3 (13) |
N2—C8—N1 | 120.7 (3) | C17—C18—C13 | 119.8 (5) |
N2—C8—S1 | 116.6 (2) | F3'—C18—H18A | 7.4 |
N1—C8—S1 | 122.7 (2) | C17—C18—H18A | 120.1 |
C7—C9—N3 | 126.7 (3) | C13—C18—H18A | 120.1 |
C7—C9—S1 | 112.6 (2) | ||
C10—N3—N4—C11 | −0.4 (4) | C10—N3—C9—C7 | −53.9 (6) |
C9—N3—N4—C11 | −174.5 (3) | N4—N3—C9—C7 | 118.9 (4) |
C6—C1—C2—C3 | −0.3 (6) | C10—N3—C9—S1 | 125.6 (3) |
C1—C2—C3—F1 | 179.2 (4) | N4—N3—C9—S1 | −61.6 (4) |
C1—C2—C3—C4 | 0.7 (6) | C8—S1—C9—C7 | −1.4 (3) |
F1—C3—C4—C5 | −179.5 (4) | C8—S1—C9—N3 | 179.0 (3) |
C2—C3—C4—C5 | −1.0 (6) | C11—N5—C10—N3 | 0.0 (4) |
C3—C4—C5—F2 | −178.4 (4) | N4—N3—C10—N5 | 0.3 (4) |
C3—C4—C5—C6 | 1.0 (6) | C9—N3—C10—N5 | 173.7 (3) |
F2—C5—C6—C1 | 178.8 (3) | N3—N4—C11—N5 | 0.4 (4) |
C4—C5—C6—C1 | −0.6 (5) | C10—N5—C11—N4 | −0.2 (5) |
F2—C5—C6—C7 | −2.0 (5) | C8—N1—C12—O1 | 5.7 (6) |
C4—C5—C6—C7 | 178.6 (4) | C8—N1—C12—C13 | −172.3 (3) |
C2—C1—C6—C5 | 0.3 (5) | O1—C12—C13—C14 | 136.8 (4) |
C2—C1—C6—C7 | −178.9 (3) | N1—C12—C13—C14 | −45.1 (5) |
C8—N2—C7—C9 | −1.0 (4) | O1—C12—C13—C18 | −43.4 (5) |
C8—N2—C7—C6 | −179.5 (3) | N1—C12—C13—C18 | 134.6 (3) |
C5—C6—C7—C9 | 136.2 (4) | C18—C13—C14—F3 | 175.8 (3) |
C1—C6—C7—C9 | −44.7 (5) | C12—C13—C14—F3 | −4.4 (6) |
C5—C6—C7—N2 | −45.6 (5) | C18—C13—C14—C15 | −1.0 (6) |
C1—C6—C7—N2 | 133.5 (3) | C12—C13—C14—C15 | 178.8 (4) |
C7—N2—C8—N1 | 179.6 (3) | F3—C14—C15—C16 | −178.2 (4) |
C7—N2—C8—S1 | 0.0 (4) | C13—C14—C15—C16 | −1.3 (7) |
C12—N1—C8—N2 | 168.8 (3) | C14—C15—C16—C17 | 2.4 (8) |
C12—N1—C8—S1 | −11.6 (5) | C15—C16—C17—C18 | −1.1 (8) |
C9—S1—C8—N2 | 0.8 (3) | C16—C17—C18—F3' | 170.2 (18) |
C9—S1—C8—N1 | −178.8 (3) | C16—C17—C18—C13 | −1.3 (6) |
N2—C7—C9—N3 | −178.7 (3) | C14—C13—C18—F3' | −169.5 (16) |
C6—C7—C9—N3 | −0.4 (5) | C12—C13—C18—F3' | 10.7 (17) |
N2—C7—C9—S1 | 1.7 (4) | C14—C13—C18—C17 | 2.3 (5) |
C6—C7—C9—S1 | 180.0 (3) | C12—C13—C18—C17 | −177.5 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···N5i | 0.94 (3) | 1.93 (3) | 2.865 (4) | 174 (3) |
Symmetry code: (i) x−1, −y+2, z+1/2. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- If you have already subscribed, you may need to register